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Usage

InChI:InChI=1/C15H17N/c1-12-3-7-14(8-4-12)11-16-15-9-5-13(2)6-10-15/h3-10,16H,11H2,1-2H3

Upstream product

• 16979-20-7 N-(4-methylbenzylidene)-4-methylaniline 
• 5398-09-4 4-tolyl benzenesulfonate 
• 104-84-7 para-methylbenzylamine 
• 3899-96-5 4-methylphenyl tosylate 
• 37100-89-3 4-chloro-benzenesulfonic acid p-tolyl ester 
• 321578-69-2 4-tolyl 4-nitrobenzenesulfonate 
• 589-18-4 4-Methylbenzyl alcohol 
• 106-49-0 p-toluidine 
• 106-43-4 para-chlorotoluene 
• 104-87-0 4-methyl-benzaldehyde 
• 124-22-1 n-Dodecylamine 
• 100-51-6 benzyl alcohol 
• 16979-20-7 (Z)-4-methyl-N-(4-methylbenzylidene)aniline 
• 59866-38-5 p-methyl-N-(p-methylbenzylidene)aniline 

Downstream Products

• 1228434-92-1 N-allyl-N-(4-methylbenzyl)-4-methylaniline 
• 857471-34-2 diethyl (p-tolyl(p-tolylamino)methyl)phosphonate 
• 394240-16-5 2-(4-methylphenyl)-4-phenyl-6-methylquinoline 
• 1422969-33-2 N¹,N⁴-bis(4-methylbenzyl)-N¹,N⁴-bis(4-methylbenzyl)fumaramide 
• 1260213-75-9 N-(4-methylphenyl)-N-(4-methylbenzyl)-N'-tosylacetamidine 
• 118072-35-8 3-(2-Dimethylaminomethyl-4-methyl-phenylamino)-propionitrile 
• 104-87-0 4-methyl-benzaldehyde 
• 16979-20-7 N-(4-methylbenzylidene)-4-methylaniline 
• 127598-71-4 N-(4-methylbenzyl) N-(2-cyanoethyl)-4-methylaniline 
• 55245-37-9 C₁₆H₁₆ClNO 

Relevant academic research and scientific papers

Enhanced Hydride Donation Achieved Molybdenum Catalyzed Direct N-Alkylation of Anilines or Nitroarenes with Alcohols: From Computational Design to Experiment

An example of homogeneous Mo-catalyzed direct N-alkylation of anilines or nitroarenes with alcohols is presented. The DFT aimed design suggested the easily accessible bis-NHC-Mo(0) complex features a strong hydride-donating ability, achieving effective N-alkylation of anilines or challenging nitroarenes with alcohols. The enhanced hydride-donating strategy should be useful in designing highly active systems for borrowing hydrogen transformations.

Photocatalytic Water-Splitting Coupled with Alkanol Oxidation for Selective N-alkylation Reactions over Carbon Nitride

Photocatalytic water splitting technology (PWST) enables the direct use of water as appealing “liquid hydrogen source” for transfer hydrogenation reactions. Currently, the development of PWST-based transfer hydrogenations is still in an embryonic stage. Previous reports generally centered on the rational utilization of the in situ generated H-source (electrons) for hydrogenations, in which photogenerated holes were quenched by sacrificial reagents. Herein, the fully-utilization of the liquid H-source and holes during water splitting is presented for photo-reductive N-alkylation of nitro-aromatic compounds. In this integrate system, H-species in situ generated from water splitting were designed for nitroarenes reduction to produce amines, while alkanols were oxidized by holes for cascade alkylating of anilines as well as the generated secondary amines. More than 50 examples achieved with a broad range scope validate the universal applicability of this mild and sustainable coupling approach. The synthetic utility of this protocol was further demonstrated by the synthesis of existing pharmaceuticals via selective N-alkylation of amines. This strategy based on the sustainable water splitting technology highlights a significant and promising route for selective synthesis of valuable N-alkylated fine chemicals and pharmaceuticals from nitroarenes and amines with water and alkanols.

Rhodium catalysts with cofactor mimics for the biomimetic reduction of CN bonds

A strategy based on the cooperation between metal and bonded cofactor mimics was applied to the transfer hydrogenation of CN bonds. We designed and synthesized a rhodium complex containing a 1,3-dimethylbenzoimidazole moiety, which could transfer hydride from a rhodium center to imine substrates in a biomimetic way. Under both transfer hydrogenation and reductive amination reaction conditions, the catalyst exhibited good selectivity towards CN bonds. With the catalyst, 34 imines were transfer hydrogenated to corresponding amines and a key intermediate of retigabine was prepared via reductive amination in a greener way. According to the NMR observations and isotope experiments, a plausible mechanism for this biomimetic reduction of CN bonds were proposed.

Hydrogenation and: N-Alkylation of anilines and imines via transfer hydrogenation with homogeneous nickel compounds

The nickel-catalyzed N-Alkylation of a variety of arylamines via transfer hydrogenation in the absence of pressurized hydrogen and basic or acidic additives was achieved in a tandem reaction. This process was further extended to the CN bond reduction and N-Alkylation of a variety of imines with ethanol, the latter acting as a hydrogen and acetaldehyde source, which allowed for the reduction and subsequent condensation to yield the corresponding N-Alkylated products.

N-Heterocyclic Olefin-Ligated Palladium(II) Complexes as Pre-Catalysts for Buchwald–Hartwig Aminations

New N-heterocyclic olefins (NHOs) are described with functionalization on the ligand heterocyclic backbone and terminal alkylidene positions. Various PdII–NHO complexes have been formed and their use as pre-catalysts in Buchwald–Hartwig aminations was explored. The most active system for catalytic C?N bond formation between hindered arylamine and arylhalide substrates was accessed by combining a backbone methylated NHO with [Pd(cinnamyl)Cl]2 in the presence of NaOtBu as a base. In these active systems evidence suggests that catalysis is mediated by colloidal palladium metal, highlighting a different coordination ability of NHOs in comparison with commonly used N-heterocyclic carbene co-ligands.

C-N Bond Formation Catalyzed by Ruthenium Nanoparticles Supported on N-Doped Carbon via Acceptorless Dehydrogenation to Secondary Amines, Imines, Benzimidazoles and Quinoxalines

Ruthenium nanoparticles (NPs) supported on N-doped carbon (Ru/N?C) were prepared by the pyrolysis of cis-Ru(phen)2Cl2 loaded onto carbon powder (VULCAN XC72R) at 800 °C. Ru/N?C NPs (0.2 mol% Ru) selectively catalyzed either acceptorless dehydrogenation coupling (ADC) or auto-transfer-hydrogen (ATH) reactions of amines with alcohols to imines and secondary amines. Such selectivity could be controlled by the choice of alkali metal ion associated with the base. Under similar catalytic conditions, the ADC cross-coupling of diamines with primary alcohols or diols afforded the corresponding benzimidazoles and quinoxalines in good to excellent yields. This catalytic system displayed good activity, recyclability, and wide applicability to a diverse range of substrates.

Application of carbon-supported ruthenium nanomaterial in preparation of N-alkyl aromatic amine compound

The invention discloses preparation and a catalytic application of carbon material supported ruthenium nanoparticles. Specifically, the average particle size of the prepared ruthenium nanoparticles isabout 2.2 nm, and the ruthenium nanoparticles are unifo

Well-Defined Amidate-Functionalized N-Heterocyclic Carbene -Supported Rare-Earth Metal Complexes as Catalysts for Efficient Hydroboration of Unactivated Imines and Nitriles

Four amidate-functionalized N-heterocyclic carbene (NHC) rare-earth metal amido complexes [(κ2-N,O-κ1-L)2REN(SiMe3)2] (L = 1-(C6H5CONCH2CH2)-3-(CH3)3C6H2(N(CH)2NC)) [RE = Er (1), Y (2), Dy (3), Gd (4)] were synthesized by one-pot reactions of 2 equiv of (1-(C6H5CONHCH2CH2)-3-(CH3)3C6H2-(N(CH)2NCH))Br (H2LBr) with 5 equiv of KN(SiMe3)3 followed by treatment with 1 equiv of RECl3 in tetrahydrofuran at -40 °C. These complexes were fully characterized, and their catalytic activities toward hydroboration of unactivated imines and nitriles were investigated, and it was found that these complexes displayed excellent activities as well as remarkable functional group compatibility for imine and nitrile substrates such as halo-, alkyl-, hydroxyl-, N,N-dimethylamino-, and nitro- substituents. Among those, the chemoselectivity for this reaction among the common unsaturated functional groups was achieved in the order CO CN > C=N > CO2Et > CC in the current catalytic system, which may facilitate their further application in synthetic chemistry.

Metal- and Base-Free Room-Temperature Amination of Organoboronic Acids with N-Alkyl Hydroxylamines

We have found that readily available N-alkyl hydroxylamines are effective reagents for the amination of organoboronic acids in the presence of trichloroacetonitrile. This amination reaction proceeds rapidly at room temperature and in the absence of added metal or base, it tolerates a remarkable range of functional groups, and it can be used in the late-stage assembly of two complex units.

One-pot reductive amination of aldehydes with nitroarenes using formic acid as the hydrogen donor and mesoporous graphitic carbon nitride supported AgPd alloy nanoparticles as the heterogeneous catalyst

Herein, we report a one-pot protocol for the synthesis of secondary amines via a tandem reductive amination of aldehydes with nitroaromatics utilizing mesoporous graphitic carbon nitride (mpg-C3N4) supported AgPd alloy nanoparticles (mpg-C3N4/AgPd) as the catalyst, FA as the hydrogen donor and water as the sole solvent, which is a protocol in harmony with the green chemistry rules. In the present one-pot catalytic reductive amination protocol, a variety of secondary amines (11 examples) were yielded by using nitroarenes as a nitrogen source and benzaldehyde in the presence of the mpg-C3N4/AgPd nanocatalyst, which is the first example in the literature. Monodisperse AgPd alloy NPs (2.5 ± 0.5 nm) were synthesized by using our established protocol via the co-reduction of silver(i) acetate and palladium(ii) acetylacetonate in the presence of oleylamine and oleic acid as surfactants in a hot organic solvent. The as-prepared AgPd alloy nanoparticles were then deposited on mpg-C3N4via a liquid phase self-assembly method. After the structural characterization of the mpg-C3N4/AgPd nanocatalyst using TEM, PXRD, BET and ICP-MS analyses, they were directly tested in one-pot direct reductive amination reactions in which they showed superior activity. The applicability of the present one-pot reductive amination strategy was demonstrated over a variety of aldehydes and nitroarenes (11 examples). Moreover, the mpg-C3N4/AgPd catalyst was a reusable catalyst in the reductive amination reactions providing 99% yield even after five consecutive runs.